Hi Molly! I’m going on a Christmas holiday with my girlfriend. We’ve slept together, but we haven’t had sex. But I think we may on this trip. If we do, it will be my first time having sex. How do I approach it? How do I start the conversation? Also, in case things heat up, any points for first time sex? ~ Nervous Newbie

Dear Newbie,

Thanks for asking this question. You’re not the first to ask it and it’s been on my to-do list for quite some time. I’m also glad you asked how you can talk to her about it, because that shows maturity and respect. While just playing it by ear can work for your first time having sex, it doesn’t ensure that you’re both on the same page, comfortable with the situation, and in the mood.

Time it right.

Ideally, this conversation happens with your clothes on and well before you’re hot and heavy. Here are some parameters you want to keep. Don’t have this conversation anywhere public. Not out to dinner. Not in the back of a cab. Do it somewhere private, where you won’t be interrupted, and you both have the opportunity to be open without others eavesdropping.

Be confident.

Be confident without being pushy. Be sure of yourself, regardless of if she says yes or no. Sure, if she turns you down, you may feel rejected, but you shouldn’t. She’s not saying np to you as a person. She’s saying no to sex. And there could be 150 reasons why. Maybe she’s experienced trauma. Maybe she’s menstruating. Or didn’t take a shower. Or maybe she’s just not ready because last time she moved too fast.

And upfront.

Being open puts you at risk for getting hurt, but it’s also what creates a safe space where you and your potential lover can be vulnerable. And vulnerability is hot. While it may feel uncomfortable, my recommendation is to just be upfront and tell her how you feel about her, your relationship, and that you’re ready if she is. Use clear and concise language: “I’ve really enjoy hanging out with you. I feel like we’re getting closer, and I like you a lot. I wanted you to know that I feel like we’re ready for sex. What do you think?”

If she says no, don’t freak out and don’t act like a hurt puppy. Instead, say something like, “No worries. Just know I like you a lot and whenever you’re ready to take it to the next step, all you have to do is say the word.”

If she hesitates, reinforce the fact that you know it’s a big decision and not one to take lightly. “I know having sex is a big step and it can be complicated. If you’re not ready, I understand. I want you to be comfortable.”

If she seems shocked, smooth it over with something like, “I really like you. And I like us. And I want to be with you. I’m nervous, too, and I don’t want to rush you. If you’re not ready, it’s okay.”

Bonus for handling it this way: It guarantees you get consent.

Talk about it.

What’s great about starting your sexual relationship by having a real conversation about intimacy, is that it gives you a smooth transition to talk about things we should all talk about before having sex with someone new. Things like contraceptives, STD testing, preferences, and hard limits that shouldn’t be crossed.

Speaking of contraceptives, be sure to bring condoms (and a water-based lubricant) with you, just in case. Always be prepared. Even if she’s on birth control, still use a condom to protect yourself for STDs and/or at her request.

couple kissing first time sex

Photo by mimi lalaa on Unsplash

Ask questions.

You want the experience to go well, and the best way to do that is to make sure you both find it pleasurable. And you can increase her pleasure by asking her what she likes and what feels good. Simple questions like, “How do you like to be touched?” or “Does this feel good? Or is this better?” or “Do you like it when I do this?” If you struggle with how to talk about sex without stumbling, download my special report on the 10 building blocks of intimate communication.

Build anticipation.

Maybe one thing leads to another after this conversation, and that’s fine. But if you have the opportunity, just hang out and relax together. Maybe go for a walk. Or have dinner (if you drink, don’t overindulge!). Delaying the sex you know is coming builds anticipation. And that leads to an increase in arousal.

Touch. A lot.

While you’re out, hold her hand. Touch her arm. Wrap your arm around her. Give her a kiss and tell her she’s beautiful. Increasing the physical contact also works toward deepening your arousal. It gets you excited and connected for the evening’s events. As things progress, so should your touching. Maybe you give her a back rub. Kiss her. Make out. Explore each other painfully slow.

Set the mood.

If you’re not already doing it by now, it’s time to set the mood. Of course, you need to have a private place. Depending on where that is, you may want to light candles or dim the lights. Maybe play soft music in the background and burn some incense. If either of you are a foodie, consider adding some fresh, juicy fruits or chocolates nearby for the two of you to enjoy.

Go slow.

Keep the pace slow. I know you’re excited. It’s your first time having sex! But the longer you can wait, the more likely you’re both going to experience more pleasure. Stay focused on each moment of the journey, not the final destination. Women, on average, need a minimum of eight minutes of foreplay before they even want to think about clitoral stimulation.  So make the moments last.

It can take 20 minutes or more of stimulation before a woman reaches climax. And chances are, you’re not going to last near that long (most penis-in-vagina sex lasts seven minutes or less, let alone first timers). So engage of lots of foreplay. And wait to move on to each step until you just about can’t stand it.

What are those steps, you may wonder? Any combination of the following will work:

Pay attention.

It doesn’t matter how much you’ve read about sex (or how many partners you’ve had), every person is different and likes different things. So pay attention to how your lover responds. Does a kiss behind her ear make her gasp? What about when you run your fingertips up her thigh? Does something make her breathing quicken or her body push toward you? If so, keep doing it! Follow her ques. And when in doubt, ask!


Once it’s all done, and your flushed and sated with a silly grin on your face, realize the night’s not over yet. Don’t just roll over and fall asleep or pick up your phone and start scrolling. Her hold close. Cuddle. Talk about it if you’d like. But giving her some aftercare and holding her close can pay off tenfold.

Other tips for the first time having sex.

That’s the basics. But here are a few other things to know about your first time having sex.

  • It’s going to be awkward at times. That’s okay. Roll with it. The first time having sex is weird for most of us. You’ll be fine.
  • Consider grooming your nether regions before the big event. You don’t have to go bald unless you want to but keeping things tidy can be appreciated.
  • Know that enthusiasm is the number one sex skill you can have. You don’t necessarily want to overdo it, but let your lover know that you are enjoying it.
  • You may be extremely turned on, but still struggle to get or maintain an erection. It’s called performance anxiety and it happens. Don’t over think it. Just relax and try again later.
  • Along these same lines, be prepared that you may not last that long. It’s been an exciting night. You’re doing it for the first time! She’s there and she’s ready and she’s soft and oh so wet. If you don’t have marathon sex, don’t worry about it. Lasting longer gets easier with practice.
  • Understand that not all sex is penis-in-vagina sex and that’s okay. Oral sex, anal sex, and manual sex are all valid and pleasurable expressions of sexual intimacy.
  • Don’t forget to have fun! Sex is supposed to be playful and lighthearted. Relax and enjoy the experience.

I sure hope that’s helpful, Newbie. I wish you the best of luck!


PS: Do you have a sex question? Email it to me at molly@yourbestsexualself.com!


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